Electronic absorption and emission spectra and computational studies of some 2-aryl, 2-styryl, and 2-(4′-aryl)butadienyl quinazolin-4-ones

Snezhana M. Bakalova, António Gil Santos, Iliana Timcheva, Jose Kaneti, Irena L. Filipova, Georgi M. Dobrikov, Vladimir D. Dimitrov

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

The relatively less popular group of quinazoline heterocyclic compounds is searched theoretically for compounds with promising classical and nonlinear optical properties, e.g. fluorescence and high (hyper)polarizabilities. Candidates for NLO materials are found among the general series of α-4-(3H)-quinazolonyl-ω-aryl polyenes 1, 2, 3 and their fluorescence spectra are registered experimentally. CIS/6-31G* calculations provide no reliable predictions of observed UV/Vis and fluorescence spectra. However, semiempirical CISD PM3 calculations predict fairly well the observed bathochromic effects arising from extension of polyene chains (CHCH) n, n=0-2, and donor substitution in the aryl fragments. The observed fluorescence is assigned to planar quinonoid S1 emissive states, while ground S0 state geometries of compounds with n=0 are nonplanar, and with n>0 are planar. We find high TDHF PM3 static polarizabilities for all studied molecules, as well as high hyperpolarizabilities β SHG and γ THG.

Original languageEnglish
Pages (from-to)229-234
Number of pages6
JournalJournal Of Molecular Structure-Theochem
Volume710
Issue number1-3
DOIs
Publication statusPublished - 26 Nov 2004

Keywords

  • α-4-(3H)-quinazolonyl-ω-aryl polyenes
  • Fluorescence
  • NLO materials
  • PM3 and ab initio calculations

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